An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols

Chemistry. 2004 Aug 20;10(16):3891-900. doi: 10.1002/chem.200400182.

Abstract

The telomerization reaction of 1,3-butadiene with alcohols to give alkyl octadienyl ethers in the presence of palladium-carbene catalysts has been studied in detail. Unprecedented catalyst efficiency with turnover numbers (TON) up to 1,500,000 and turnover frequencies (TOF) up to 100,000 h(-1) have been obtained after optimization for the reaction of methanol in the presence of an excess of in situ generated carbene ligands. High yields (75-97 %) and catalyst productivities (TON 15,000-100,000) are observed for other aliphatic alcohols and phenols. For comparison five carbene-palladium(0) complexes have been synthesized and characterized by X-ray crystallography. Both electronic and steric effects on the stability and reactivity of the catalysts have been discussed on the basis of density functional theory calculations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Alcohols / chemistry*
  • Butadienes / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism
  • Time Factors

Substances

  • Alcohols
  • Butadienes
  • Ligands
  • Organometallic Compounds
  • Palladium
  • 1,3-butadiene